7-(cyclopentyloxy)-2H-chromen-2-one | 946169-95-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(cyclopentyloxy)-2H-chromen-2-one
• 英文别名: 7-Cyclopentyloxychromen-2-one
• CAS: 946169-95-5
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: VKFUWGOLLXHFIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-碘-1,1,1-三氟乙烷 、 7-(cyclopentyloxy)-2H-chromen-2-one 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以80%的产率得到7-(cyclopentyloxy)-3-(2,2,2-trifluoroethyl)-2H-chromen-2-one
  参考文献：
  名称：

  Visible-Light-Induced Direct Csp²-H Radical Trifluoroethylation of Coumarins with 1,1,1-Trifluoro-2-iodoethane (CF₃CH₂I)

  摘要：

  DOI：

  10.1021/acs.joc.0c02739
• 作为产物：
  描述：

  溴代环戊烷 、 7-羟基香豆素 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.42h， 生成 7-(cyclopentyloxy)-2H-chromen-2-one
  参考文献：
  名称：

  Pancreatic anticancer activity of a novel geranylgeranylated coumarin derivative

  摘要：

  A series of hydroxycoumarin derivatives has been synthesized and evaluated against human pancreatic PANC-1 cancer cells under nutrient-deprived conditions. Several compounds exhibited 100% preferential cytotoxicity at low micromolar concentrations under nutrition starvation, and showed no cytotoxicity under nutrient-rich conditions. In this study, a novel geranylgeranylated ether coumarin derivative 9 was found to exhibit the highest cytotoxic activity of 6.25 mu M within 24 h. The preferential anti-tumor activity exhibited by compound 9 against PANC-1 under low oxygen and nutrient environment illustrates its great potential as a promising lead structure for the development of novel agents to combat pancreatic cancer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.005

文献信息

• COMPOUNDS FOR TREATING SPINAL MUSCULAR ATROPHY
  申请人：PTC Therapeutics Inc.

  公开号：US20150119380A1

  公开（公告）日：2015-04-30

  Provided herein are compounds, compositions thereof and uses therewith for treating spinal muscular atrophy. In a specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN2 into mRNA that is transcribed from the SMN2 gene. In another specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 into mRNA that is transcribed from the SMN1 gene. In yet another embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 and SMN2 into mRNA that is transcribed from the SMN1 and SMN2 genes, respectively.

  本文提供了用于治疗脊髓性肌萎缩症的化合物、其组合物及与其一起使用的用途。在一个具体实施例中，本文提供了一种可以用来调节SMN2基因转录的mRNA中包含外显子7的形式化合物。在另一个具体实施例中，本文提供了一种可以用来调节SMN1基因转录的mRNA中包含外显子7的形式化合物。在另一个实施例中，本文提供了一种可以用来调节SMN1和SMN2基因转录的mRNA中包含外显子7的形式化合物。
• A general photo-induced wide-scope regioselective hydroboration of alkenes without using a photocatalyst or an external initiator
  作者：Yu-Qi Miao、Xin-Ying Li、Qiao-Jing Pan、Yubin Ma、Jia-Xin Kang、Yan-Na Ma、Zhenxing Liu、Xuenian Chen

  DOI：10.1039/d2gc02313j

  日期：——

  Despite the recent development of boryl radical reactions, current methods to generate them by relying on photocatalysts or radical initiators cause contamination of the reaction. Herein, a novel system for generating boryl radicals has been developed without using photocatalysts or external radical initiators, and only a catalytic amount of thiol has been used. The success of this approach depends

  尽管硼基自由基反应最近得到发展，但目前依靠光催化剂或自由基引发剂产生它们的方法会导致反应受到污染。在此，已经开发了一种用于产生硼基自由基的新系统，而无需使用光催化剂或外部自由基引发剂，并且仅使用了催化量的硫醇。这种方法的成功取决于硫醇作为质子供体和氢原子转移 (HAT) 催化剂的双重作用。硫醇首先与 NHC-硼烷反应，通过脱氢偶联反应生成硼基硫化物，然后它们就地发生通过光化学反应裂解它们的 B-S 键。获得的自由基随后参与快速硫醇催化的 HAT 反应，得到硼氢化产物。该策略使区域选择性硼氢化能够以良好至优异的产率从多种α，β-不饱和烯烃和苯乙烯大规模合成α-或β-硼化产物，在室温下具有广泛的官能团相容性。该反应还可以扩展到亚胺的自由基型亲核加成。这种前所未有的协议有望通过光化学反应使用硫化硼，在其他涉及硼自由基的反应中找到潜在的应用。
• US9617268B2
  申请人：——

  公开号：US9617268B2

  公开（公告）日：2017-04-11
• Visible-Light-Induced Direct Csp²-H Radical Trifluoroethylation of Coumarins with 1,1,1-Trifluoro-2-iodoethane (CF₃CH₂I)
  作者：Xiaoyu Chen、Linlin Li、Congcong Pei、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1021/acs.joc.0c02739

  日期：2021.2.5
• Pancreatic anticancer activity of a novel geranylgeranylated coumarin derivative
  作者：Tehsina Devji、Claire Reddy、Christina Woo、Suresh Awale、Shigetoshi Kadota、Dora Carrico-Moniz

  DOI：10.1016/j.bmcl.2011.08.005

  日期：2011.10

  A series of hydroxycoumarin derivatives has been synthesized and evaluated against human pancreatic PANC-1 cancer cells under nutrient-deprived conditions. Several compounds exhibited 100% preferential cytotoxicity at low micromolar concentrations under nutrition starvation, and showed no cytotoxicity under nutrient-rich conditions. In this study, a novel geranylgeranylated ether coumarin derivative 9 was found to exhibit the highest cytotoxic activity of 6.25 mu M within 24 h. The preferential anti-tumor activity exhibited by compound 9 against PANC-1 under low oxygen and nutrient environment illustrates its great potential as a promising lead structure for the development of novel agents to combat pancreatic cancer. (C) 2011 Elsevier Ltd. All rights reserved.